Mentorship Troubles: Finding the Right Fit

Astika Gupta

Sr Product Manager at eBay



I love mentoring. I do mentoring at Plato and elsewhere and I am enjoying every bit of it. One of the biggest challenges that troubles most mentees is how to find a mentor who would be the right fit for them.

Mentors and mentees may come from different backgrounds and have different histories or preferences. While most mentors have abundant experience and lessons to share, that may not be something that a particular mentee is looking for.

Actions taken

When I was a mentee myself, before rushing to choose a mentor, I would spend some time self-reflecting and learning about myself and my problems. I would ask myself, “What is a challenge that I need the most help with?” Is it a specific work-related problem or something that has to do with some long-term skills such as public speaking, networking with peers, leading a meeting, etc? Also, I was a couple of times at a career crossroads when I had to choose the right career path and wondered how to get from A to B. The right mentor is the most valuable something that can happen to a person in that kind of situation.

Once you have listed all your questions/problems, it would become more obvious that one mentor likely wouldn’t be able to answer all of your questions. Take that list and start to prioritize. How big of a pain point is it? How quickly could it be resolved? How important is it for your career? Some of these questions may help with prioritization. Once you have compiled a prioritized list, you should start mapping out mentors. You may find someone who would be able to help you out with problems B and D, but not A or C. Stick to your priorities. If B and D are more important than A and C, that is the right mentor for you.

After you have defined your problem(s), seek mentorship opportunities. Plato is one of the mentoring sites that is targeting engineering and product leaders. But, depending on where you are in your career and what you want to do, some other types of mentorship could be beneficial. One thing I did, especially when I was transitioning to a PM role, was to find people on LinkedIn with the same professional aspirations and cold email them. I would write to them to ask them how they transitioned from software development to product management and though the response rate was not quite impressive, the first-hand experience was invaluable.

By now, you should have mapped out three to four mentors who can help with the most important problems. I would have a few initiation calls to screen a mentor -- and have them screen me -- succinctly describing the problem and learning if their approach would be the right for me. Sometimes one call would be sufficient to tell if the two of you are the right fit, but sometimes it may take longer, like in any other relationship-building situation.

Also, look at different alternatives. Experienced leaders within your company, but in the other department, could often be a great fit, being familiar with the company context. Many companies also have formalized mentorship rings of less formal coffee chats, something I benefited from a great deal while working at Microsoft. Also, Facebook groups could be a good starting point to connect with people who can help you.

Lessons learned

  • Understanding avenues of how and when to connect sometimes should precede who to connect with, which would become more clear through self-reflection. Knowing yourself is the first step toward a successful mentorship relationship.
  • Not every problem is the same and mentors can’t help with all of them. Developing soft skills is the most demanding timewise. To become confident in public speaking, or to become a great storyteller may take much more time than solving a more specific technical challenge. I usually don’t expect my mentors to help me with soft skills because acquiring those skills requires continuous practice and not a mind-shift conversation. Mentors can be of greater help if they can share their knowledge, their perspective, or lived-through experience and help you with a mind-shift change.

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Astika Gupta

Sr Product Manager at eBay

Leadership DevelopmentCommunicationOrganizational StrategyDecision MakingCulture DevelopmentEngineering ManagementMentorship ProgramsTechnical ExpertiseCareer GrowthCareer Progression

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